Daydream in Blue
by F. F. Nightingale
Summary: AU. Olivia, a morally gray specialist, is tasked with seducing the President of the United States. To her misfortune, it goes well.
1. Chapter 1

**Chapter 1**

She was sipping Bordeaux from her wine glass, eyes glued to her flat screen when the text tone went off. Before grabbing the phone, her eyes dropped to her watch.

 **2:18 A.M.**

She grimaced. Texts at this hour usually didn't mean good news.

Leaning forward, she picked up her cell. Upon reading the number, her frown deepened.

 _Hamptons in Columbia tomorrow. 3PM. My treat._

She reread it two times before discarding the phone on the couch.

Five minutes passed. The rerun of the criminal drama failed to hold her attention. She scanned her living room, pausing when she located the bottle of wine. Half of the contents still remained. Snatching the bottle, she peered at the liquid. Without hesitation, she brought it to her lips and downed the contents in under thirty seconds.

 _He never comes to me. I always go to him._

This stray thought replayed in her head until the drowsiness kicked in.

She passed out on the couch ten minutes later.

x_X_x_X_x

By 2PM, the day was humid. She considered wearing lighter clothing, but that would give him an excuse to look at her longer than necessary. Talking to him was nauseating enough.

She chose a pair of dark jeans and a gray button up shirt. For good measure, a black cardigan overtop.

At a quarter to three, she pulled up to the hotel. After mentioning her name to the valet, she left him her keys and sought out the outdoor restaurant on the 18th floor. As she rode the elevator up, she pretended her heart wasn't pumping faster than usual. She also pretended she was happy. If this meeting meant what she thought it did, it'd be an extra few grand in her pocket. Maybe even five digits. As much as she loathed him, he had a habit of paying her well.

It wasn't difficult to spot him. He lounged in a chair at the furthest table from the bar, eyes glued to his phone. She tried not to be shaken by the fact that the entire restaurant was empty. In fact, other than a bartender wiping down some wine glasses, the terrace was completely empty.

 _Just get this over with._

She approached him with a smile that made her lips ache. When she was only a few feet away, he finally looked up.

"Miss Pope, what a lovely surprise!" He pocketed his phone and stood, offering her his large hand.

Reluctantly, she shook it, making sure to maintain eye contact with him. He hated when her attention wasn't on him during conversation.

"Mr. Doyle, a pleasure," Olivia said.

 _Surprise my ass. You knew I'd come._

"Sit, sit," he gestured, falling back into the chair. "Haven't seen ya in a coon's age. Not since...oh, what was it...the job in Boston. Paid ya a pretty penny for that too."

"You did," she agreed, evening out her expression. "I was surprised to get your text. I thought you said Boston was the last time you'd need my services."

Hollis laughed heartily, shaking his head.

"Sweetheart, me too. If my people were more competent, Boston woulda been the last you heard from me. Though, can't say it's all bad. I get to see your pretty face."

Her smile slipped back on. "That's kind of you."

Years of dealing with this man allowed her to sound genuinely thankful for the compliment.

"Much as I'd love to catch up, I got a proposition for ya."

"Am I allowed to say no?"

His next laugh was louder than the one before. Olivia wanted to punch the smugness off his face.

"Course ya are, honey. Don't know why ya would."

The grin he wore disappeared in the blink of an eye.

"What can I do for you?" she asked politely.

Hollis studied her with a hard squint. She didn't sever his gaze, instead, attempting to appear bored. She knew it was a pet peeve of his. Surrounded by people who hung on to his every word, Hollis Doyle hated apathy. That emotion came to Olivia naturally and she utilized it whenever she could around the man, if only to ruffle his feathers.

"Let me buy ya something to drink," he finally said. "Whiskey on the rocks, if I remember correctly?"

She didn't protest as he barked out her order to the bartender. A minute later and the bartender set the glass down in front of her.

"That'll be all," Hollis dismissed.

His lack of an alcoholic beverage uneased her, but before that unease could surface, she took a sip from the glass, enjoying the burn coursing through her.

"In all the years we've known each other, can ya believe I've never asked about your political affiliations?"

Olivia shrugged. "I figured you wouldn't like my answer."

"That sounds suspiciously Democratic."

She didn't answer, instead, taking another sip from her glass.

"Speak freely, Olivia. I won't get offended."

Her brows rose at this.

"Scout's honor," he said, raising a hand.

"Freely," she repeated. "Politics haven't been for the people in a long time. I rarely participate. As the saying goes, if voting changed anything, they'd make it illegal."

Hollis seemed surprised. "Never viewed you as a cynic."

 _That's because you know nothing about me._

"Can you blame me?"

"S'pose not," he agreed, tapping his fingers arrhythmically against the table. "I'm glad you're objective about this platform. It'll make the assignment I'm givin' ya that much easier."

She downed the rest of her drink before speaking.

"That assignment being?"

He didn't immediately respond, instead, opting to pull a folder out of a black briefcase by his feet.

"How's Miss Whelan's case goin'?"

Stunned, Olivia redirected her gaze to her lap. Inhaling slowly, she composed herself with a tight smile.

"Fine."

Hollis eyed her with a raised brow.

"Don't get me wrong, you're a miracle worker. But I don't think even you got the capacity to get her off."

Olivia clasped her hands together. Tight.

"I didn't realize you were checking up on me."

He shrugged. The smile he wore was one of his more disingenuous ones.

"You're an important friend to me, Olivia. I like knowin' what's goin' on in your life."

 _What a load of shit._

"Miss Whelan's case is a work in progress."

He chuckled, but the sound never left his throat.

"Murder's a tough sell on a jury, even if it's justified. The prosecutor will tear her apart soon as they grill her on the amount she drank that night."

Olivia debated on how to respond. Hollis bringing Abby Whelan up wasn't unintentional. The fact that he knew some of the more sensitive details of the case, all but confirmed this. Unfortunately, she couldn't figure out what his motive was. To intimidate her? Make it known he kept tabs on her?

"You're probably wonderin' Miss Whelan's relevance to the conversation."

She nodded, not trusting herself to speak. Her own emotions were tangled up in the case. The last thing she needed was for Hollis to know that.

"Upon your acceptance of this assignment, as a show of good faith, I'll ensure Miss Whelan is released within the week."

Her shock was brief. Suspicion, a lifelong friend, immediately re-examined what was just said.

"What's the assignment?"

Ultimately, that's what it came down to. Hollis knew, despite his intimidation tactics, that she still had the capability to turn the assignment down. Abby was a bargaining chip. Sadly, it was a damn good one.

Wordlessly, Hollis offered her the folder. Olivia stiffly took it and thumbed it open.

The content was unexpectedly dull compared to what her imagination conceived. She was expecting something illegal; cartels, traffickers, black market activity as the worst case scenario.

Instead, paper-clipped to the first page was a photo of the President of the United States. Olivia couldn't immediately recall his name. She hadn't been lying when she told Hollis politics weren't an arena she frequented with.

The paper his photo was attached to, clarified her ignorance.

 **Fitzgerald Grant III.**

 **48.**

 **Spouse: Mellie Grant.**

 **Children (1): Jerry Grant Jr.**

Olivia continued reading the first page, brows drawing together. It was nothing more than general information about the President and his family. Information anyone could pull off the internet.

"I don't get it," she said, looking up after finishing the page. "If you're looking to get him assassinated, you've grossly misjudged my capabilities."

Hollis's full-bellied laugh momentarily caught the attention of the bartender. Olivia patiently waited for it to recede.

"Oooh, that's a good one," he remarked, wiping at his eye. "You should know by now, I got qualified people for that."

She knew, but it was a fact about him she chose to ignore for the sake of her conscience.

"No, my request is much more harmless. I'd like ya to get to know President Grant."

Her eyes dropped to the file.

"I just did."

He wasn't amused by the blatant answer. His narrowed gaze said as much.

"My confidants in the White House tell me President Grant and his wife have yet to sleep in the same bed. In fact, her bedroom's in the opposite wing from his. 'Course they play happy couple for the cameras."

Olivia didn't like where this conversation was heading.

"Their marriage is on the rocks," he continued. "Hell, probably been that way long before he secured the White House. Naturally, I can't decline the opportunity to capitalize on this information."

He stared at her without blinking. "I'd like you to get to _know_ President Grant."

Her mouth dropped open. "Mr. Doyle-?"

"Back to formalities? Olivia, we know each other better than that."

He was cornering her. If his words weren't doing so, his unwavering gaze certainly was.

"If I'm to understand correctly," she sounded out, "you want me to what- _seduce him_?"

"Seduce him, tempt him, lasso his libido- I hardly care what you wanna call it. Ensure things between you two become intimate and on top of helping you out with Miss Whelan, I'll deposit a cozy two million in your bank account."

The number lingered in her head much longer than she was proud of. Then again, she had never been offered such a significant amount of money before. Two million. It was enough to provide much needed renovations to her life.

"This is the President of the United States," Olivia stated. "What makes you think he'd ever let his guard down enough to cheat on his wife?"

"Callin' Mellie Grant his wife is like callin' a whore an angel," Hollis said, unperturbed by her skepticism. "And let's just say he's been known to have a wandering eye."

For the first time in a long while, Olivia was speechless. She had never considered herself a holier than thou person. In fact, a majority of her past actions could be considered morally gray at best, borderline unethical at worst. All done for a paycheck. Which probably made her a worse person. But she'd accepted those feelings about herself long ago. The world wasn't always fair, she learned early on. You either adapt or you die. She chose to adapt.

Accepting this assignment would twist her moral compass into uncharted territory.

She wasn't new to flirtation. Some of her best paychecks were earned through adopting a doe-eyed, damsel in distress persona. Men seemed to love playing the role of knight in shining armor.

However, none of the encounters ever resorted to sexual relations. She had a limit to what she was willing to do to achieve her, and indirectly, her employer's goals. That's a part of what made her so efficient. Rarely did she ever need to get her hands dirty.

This assignment would not only dirty her hands, but pollute what little ethics she still had.

Was it worth it?

 _Abby will be free. She doesn't deserve to rot in prison for half of her life._

Loathe as Olivia was to admit it, Hollis was right. The prosecution had a sturdy case because Abby indulged in a few drinks earlier in the day prior to killing her abusive bastard of a husband. That wasn't something she could fix no matter the amount of bruises and injuries Abby showed the jury.

 _Two million. It's enough to relocate. Leave this life behind._

Olivia closed her eyes. It'd been a while since she despised herself this much. To not only consider accepting, but know deep down, it was out of selfishness.

And that's why Hollis Doyle went to her, she realized. Give this assignment to a less ethical person than her and he ran the risk of Grant not falling for the bait. Give the assignment to someone more ethical than her and he ran the risk of Grant finding out he was being set up.

In some ways, she was neutrality personified. And Hollis knew exactly what to offer so she didn't stray from this alignment.

"Gonna need an answer soon, sweetheart."

Her eyes slid open, landing on the open folder.

 _He's handsome, I'll give him that._

Unwilling to decipher her conflicting feelings any further, Olivia exhaled.

"I accept."


	2. Chapter 2

**Chapter 2**

Before Olivia arrived at _Leon's_ _Diner_ , she texted him.

 ** _12-21-95_**

By the time she found a parking spot behind the restaurant, she received one back.

 ** _Patterson, IL_**

Relieved he was free to see her, she entered the diner and chose her usual booth in the corner furthest from the door. She ordered a glass of water filled to the brim with ice cubes. While she waited, she absently chewed on them.

The past few days, she'd been debating on what to tell him. Anytime she dealt with Hollis Doyle, he became her confidant. Long ago, they'd agreed the politician was not to be trusted, no matter how monetarily kind he could be. Should something happen to her, he'd know who was responsible. It was a safety net; the only one Olivia was willing to cast. She trusted him with her life.

She noticed him enter just a few minutes shy of ten in the evening. While he searched for her, she admired the tailored, indigo suit and dressy black shoes he wore. It'd been three months since they'd last spoken in public. She forgot just how impeccable his fashion sense had become.

 _Clearly, he's finding better clients than I am._

He located her a moment later and she beckoned him over with a luminescent smile. This was another luxury afforded from seeing him again. She rarely had to fabricate her emotions.

"Liv," he greeted, slipping into the opposite side of the booth.

"Harrison."

She extended a hand and he slipped his into it.

"It's good to see you," she said.

They detached their embrace and waited for the waitress to arrive. In under five minutes, his hands were secured around a mug of steaming black coffee.

"Long night ahead of you?" she asked after their waitress had departed.

"If I locate my client's hundred grand by tomorrow night, I get to keep a quarter," he said. "Can't afford to sleep."

"How is it you always get the easy cases?"

He threw her a disbelieving look. "Easy? I haven't slept in three days."

With that, he downed half of the mug in one go.

She looked on, impressed. "Okay, point taken."

"How bout you? Any luck on the Whelan case?"

Frowning, she studied the condensation forming on her glass.

"She's being released on the 13th."

"Released?" He examined her closely. "As in released, released?"

"Yes."

"How'd you manage that? Not that I doubt your ability to get business done. You're a pro. But from what I read in the paper, the chance of acquittal looked grim."

"I had help. Hollis Doyle."

Harrison quickly peered around the diner before leaning forward.

"Liv, you're better than that. Don't tell me you got him involved."

"Of course not," she replied, lowering her voice. "I'd sooner deal with terminal cancer than ask him for a favor."

The disgust on her face calmed Harrison somewhat.

"How's he involved?"

"He came to me with an assignment. To entice me into saying yes, he offered to help exonerate Abby."

"Seeing as she's being released, you said yes?"

She detected a hint of frustration in his voice, but couldn't fault him for it.

"After I finish the assignment, he's paying me two million."

Harrison froze. "Two million?"

She nodded.

Whistling, he took another drink from his mug.

"It's not an amount I could say no to."

He considered her response for a moment.

"I don't know I'd be able to say no either."

They sat in silence for a few minutes, temporarily losing their thoughts to the soft murmurs of dispersed clientele in the diner and the angry, Spanish shouts flying out of the kitchen.

"You know I gotta ask."

"I know."

Before he could interrogate her further, she pulled out a folder and slid it across the table.

Harrison busied himself with the contents inside. She watched him read over the general information of the President, as she had done days prior. His confusion was much more detectable than hers had been.

"Turn the page," she suggested after he threw her a perplexed look.

Harrison obeyed.

"No way this is his."

He picked up the platinum credit card, rereading Hollis Doyle's name on front.

"It's a way for him to control the assignment. Paying for the hotel and anything else I need lets him know where I am at all times."

"Why?" He looked up. "He's always given you distance to do your thing."

She didn't answer, instead, opting to gaze out the window.

Harrison returned to the folder.

"Round way trip to DC," he read, bringing the plane ticket closer to his eyes. "Departing the 13th. That's the day after tomorrow."

His eyes fell onto the RSVP slip.

"Is that what I think it is?"

This time, he waited for her to respond.

Containing a heavy sigh, Olivia turned back to him.

"Yes."

"You know the kind of people you have to rub shoulders with to get invited to this event?" He fingered the outline of the silver, engraved invitation. "It's nearly impossible unless you're a higher up in DC."

His own statement ushered in an epiphany. "Doesn't the President always attend?"

She smiled, but it failed to reach her eyes.

"Yes."

Harrison re-observed the contents of the folder.

"What exactly is Doyle having you do?"

She struggled to answer without sounding guilty.

 _You'll never have to admit this to anyone other than him. Just this once. As a fail-safe, he has to know._

"He wants me to get intimately acquainted with President Grant on the evening of the gala. Didn't say why, but it's obvious he wants him distracted."

Harrison stared at her, expression unreadable.

"No judgment," she said, unafraid to return his stare. "We agreed when we started doing this."

"Liv-."

"No judgment."

It was clear he had a lot to say, but mercifully, he stood down. Instead, his focus returned to the folder.

A second later and she was surprised to hear him expel a wry laugh.

"What?"

"It's funny when I think about it," he admitted, shaking his head. "My childhood friend, Olivia Pope, is going to seduce the President of the United States."

Reluctantly, she grinned as well.

"Funnier too is Doyle hiring you to do it. You're not exactly the seducing type."

She knew he meant no ill will in voicing this. Seduction was not a skill she held in her arsenal.

"That's probably what's making me the most nervous. I mean, what if he doesn't like-." She gestured down at herself.

"What's not to like? You're an intelligent, beautiful black woman. If he doesn't like that, it's a helluva loss on his part."

She arched a brow. "Beautiful? Why Harrison, I never knew."

He shrugged. "Just stating it like I see it. A word of advice- try being confident around him. I've worked enough around his type. Powerful, controlled, wealthy. They respect confidence. You'll get him to notice you that way."

"Maybe Doyle should've hired you."

"Got his number?"

That he could help make light of such a serious assignment brought Olivia some much needed relief. Her mind had been on this assignment day and night, both willingly and unwillingly. Concerns too personal to speak with Harrison about, flooded her at the most inopportune times. Taking out the trash. Soaking in a bath. Picking up groceries.

With a joke, Harrison reminded her of something essential. No matter how the assignment turned out, she at least had him.

"What are you gonna wear?"

She plucked an ice cube from her glass and popped it in her mouth.

"Dunno. That's important, isn't it?"

"Considering you dress like a middle school teacher, yeah."

Suppressing a smile, Olivia continued chewing on the ice until it was melted.

"Before the gala, I'm going to do some shopping. It's the only part of this assignment I'm looking forward to. Wounding Doyle's bank account."

"I'll look into some shops in DC," he promised, pulling out his cell. "A friend of a friend owns a chain of gown boutiques up there."

"Thank you, Harrison."

"If you're gonna be doing this, you're gonna look damn good doing it."

When he finally pocketed his cell, Olivia decided to bring up the second topic of conversation she'd been meaning to have with him.

"I have a favor to ask."

"Prior to tonight, I didn't think you could surprise me," he said. "I'm all ears."

"Abby Whelan is going to be staying at my apartment. I don't know how long yet. I'm planning to pick her up the morning of the 13th."

"Need me to play babysitter?"

"You don't have to check in every hour," Olivia assured. "Just give her a call once a day and ask how she's holding up. She's going to be a little frail. I don't want to leave her entirely alone."

"Consider it handled."

She gazed at him for a long moment. "What the hell did I do to get such a good friend?"

"Nothing," he answered. "You think I should start charging you?"

"Only if you want payment in the form of cheap wine and Bobby Womack albums."

x_X_x_X_x

Olivia rechecked her luggage for the third time.

"I still don't understand," Abby said, following her into the bedroom. "I mean I'm grateful-."

She peered down at her feet, twiddling her hands nervously.

"I just-I don't know how you did it. And you haven't been very clear with me."

Olivia turned around. "Do you regret me clearing you of murder?"

Her eyes widened. "Of course not. You know that's not what I mean."

"Then what do you mean?"

She felt slightly bad watching Abby fumble for a response. Since her arrival, the woman had been walking on egg shells around her. Olivia attributed it to a mix of gratitude and disbelief. As optimistic as she'd tried to appear during their meetings in prison, Abby wasn't naive enough to ignore the improbability of acquittal. It was clear she was still in a daze from the verdict.

Her persistent questions didn't help the matter. Olivia still hadn't conjured up a believable answer as to how she'd done it. For obvious reasons, the truth was off-limits.

"I'm sorry." She lowered her head. "I probably sound like an ungrateful bitch."

Olivia gently approached her. "You don't. I understand you're still taking it in. When I return from DC, I'll explain it further, okay?"

"Yeah, okay," Abby agreed, attempting a smile. "Can you at least tell me why you're being nice enough to let me stay at your place? Don't get me wrong, I like you, but I don't, you know..."

She gestured her head at Olivia's unmade bed.

Containing the urge to laugh, Olivia answered, "Rest assured, you're not gonna wake up with me trying to crawl into bed with you."

"If it's any consolation, I'd choose you over my ex."

This time, she didn't bother keeping back her amusement.

"That's kind of you, Miss Whelan."

"It's Abby." She straightened up. "You got me off for murder. I think we can call each other by first name."

 _She sure rebounds quick. Maybe being on her own won't be so bad._

"Local news stations will be staking out your house," Olivia explained, grabbing the handle of her luggage. "The outcome of the trial wasn't exactly favorable to everyone. If anything, think of it as a safety precaution."

Abby bit her lip and nodded.

"A friend of mine named Harrison is going to be ringing here everyday to check in. His number's also on my fridge. If you need anything, call him."

"What about you?"

"I'll be-."

 _Up to no good._

"-indisposed," Olivia finished. "I have business in DC. It shouldn't take more than a week."

"Okay."

Before she exited her apartment, Olivia paused beside Abby's rigid form. Though they were on first name basis, she wasn't sure if they were friendly enough to embrace. The only other person she did this with was Harrison. Despite being in contact twice a week for three months, she wasn't yet sure how to handle parting with the woman. Especially outside of a prison cell where their relationship had been nothing more than hired specialist and client.

"Take care of yourself, Abby," Olivia said, offering up her hand.

She clasped it lightly. "Thank you. I'll find a way to pay you back for this."

"Think nothing of it. Try to relax this week."

She offered the young woman a smile. Abby attempted to return it, but it got buried behind a series of sniffles as she wiped one teary eye with the back of her hand.

 _The plane leaves in less than an hour._

Olivia turned and marched to the front door, ignoring the guilt eating away at her. She'd never been good at comforting people, especially when they cried. Long ago, she'd learned to stifle her own negative emotions to the point that they passed with the ease of a minor headache. She could offer Abby nothing, even if she wanted to. Worse, she couldn't help but ask herself why the woman couldn't bury her pain like she'd been taught to do.

 _I can't be like this around Grant. He'll never lower his guard._

Throughout her four hour journey to DC, Olivia again debated how to best go about seducing the President. Almost every scenario suggested she adopt a version of herself she wasn't sure she was capable of being.

 _Two million. Two million. Two million._

By the time the plane touched down, a semblance of a plan finally began to form.


End file.
